DE182218C - - Google Patents
Info
- Publication number
- DE182218C DE182218C DENDAT182218D DE182218DA DE182218C DE 182218 C DE182218 C DE 182218C DE NDAT182218 D DENDAT182218 D DE NDAT182218D DE 182218D A DE182218D A DE 182218DA DE 182218 C DE182218 C DE 182218C
- Authority
- DE
- Germany
- Prior art keywords
- nitrotoluene
- mercury
- compound
- product
- hydrochloric acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- PLAZTCDQAHEYBI-UHFFFAOYSA-N 2-nitrotoluene Chemical compound CC1=CC=CC=C1[N+]([O-])=O PLAZTCDQAHEYBI-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 claims description 6
- 229910000474 mercury oxide Inorganic materials 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 3
- 229940100892 mercury compound Drugs 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 239000002244 precipitate Substances 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 150000002731 mercury compounds Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 235000011121 sodium hydroxide Nutrition 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 229910052753 mercury Inorganic materials 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- VLZLOWPYUQHHCG-UHFFFAOYSA-N nitromethylbenzene Chemical compound [O-][N+](=O)CC1=CC=CC=C1 VLZLOWPYUQHHCG-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940101209 mercuric oxide Drugs 0.000 description 1
- CBBVHSHLSCZIHD-UHFFFAOYSA-N mercury silver Chemical compound [Ag].[Hg] CBBVHSHLSCZIHD-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229940100890 silver compound Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/10—Mercury compounds
- C07F3/12—Aromatic substances containing mercury
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- JVI 182218 KLASSE 12o. GRUPPE- JVI 182218 CLASS 12o. GROUP
Zusatz zum Patente 182217 vom I.Dezember 1905.Addendum to patent 182217 of December I, 1905.
Patentiert im Deutschen Reiche vom 13. Februar 1906 ab. Längste Dauer: 30. November 1920.Patented in the German Empire on February 13, 1906. Longest duration: November 30, 1920.
Durch das Patent 182217 wird ein Verfahren zur Darstellung einer quecksilberhaltigen Verbindung aus o-Nitrotoluol geschützt. Das nach diesem A-'erfahren erhältliche Produkt bleibt in der Reaktionsflüssigkeit gelöst. Es enthält, wie die Analyse ergab, auf einen Rest des o-Nitrotoluols ein Atom Quecksilber. Bei Versuchen, welche in der Absicht angestellt wurden, durch längere Reaktionsdauer eine bessere Ausbeute an diesem Produkt zu erhalten, zeigte es sich, daß die lösliche Substanz allmählich fast vollständig verschwindet und an ihrer Stelle ein in der Reaktionsflüssigkeit schwer löslicher Körper entsteht, welcher sich dem unangegriffenen Quecksilberoxyd beimengt. Die Bildung dieser Verbindung beginnt schon nach verhältnismäßig kurzem Kochen, doch nimmt ihre Menge beständig zu, ohne daß es bisher gelungen ist, das Nitrotoluol vollständig in Reaktion zu bringen.Patent 182217 provides a method for the representation of a mercury-containing compound from o-nitrotoluene protected. The product obtainable according to this A method remains dissolved in the reaction liquid. As the analysis showed, it contains on one The remainder of the o-nitrotoluene is one atom of mercury. In attempts which are made with the intention of doing so were to obtain a better yield of this product by a longer reaction time, it was found that the soluble substance gradually disappears almost completely and a body that is difficult to dissolve in the reaction liquid arises in its place, which is added to the unaffected mercury oxide. The formation of this connection begins after a relatively short boil, but its amount increases steadily to, without it has so far been possible to bring the nitrotoluene completely into reaction.
Die neue Verbindung enthält auf einen Rest des Nitrotoluols zwei Atome Quecksilber. Zu ihrer Darstellung verfährt man zweckmäßig folgendermaßen.The new compound contains two atoms of mercury for one residue of nitrotoluene. To represent them, one proceeds appropriately as follows.
Beispiel: 30g o-Nitrotoluol (1 Mol.Gew.), 95 S gefälltes Quecksilberoxyd (2 Mol. Gew.) und ι 1 1,8 prozentige Natronlauge (entsprechend etwa 2 Mol. Gew. NaOH) werden amExample: 30g o-nitrotoluene (. 1 M.W.), 95 S precipitated mercuric oxide (.. 2 mol wt) and 1 ι 1.8 percent sodium hydroxide solution (corresponding to about 2 mole percent NaOH..) Are most
Rückflußkühler im Ölbad 30 Stunden lang gekocht, darauf die Flüssigkeit von dem Niederschlag getrennt und letzterer durch Ausäthern oder Wasserdampfdestillation von dem darin suspendierten Nitrotoluol befreit. Das Produkt enthält außer der neuen Queck-Silberverbindung des ο - Nitrotoluols noch unverändertes Quecksilberoxyd und geringe Mengen Quecksilber. Man digeriert das Gemisch mit 10 prozentiger Salzsäure in .der Kälte, wodurch das Quecksilberoxyd gelöst und das Reaktionsprodukt in sein äußerst schwerlösliches hellgelbes Chlorid übergeführt wird. Aus letzterem gewinnt man durch Erhitzen mit sehr verdünnter Natronlauge wieder die freie Quecksilberverbindung. Um diese vollständig rein zu erhalten, digeriert man sie längere Zeit mit überschüssiger kalter 10 prozentiger Essigsäure und erhält nach eventueller Filtration eine hellgelbe klare Lösung, welche das Acetat der neuen Verbindung enthält. Wird diese Lösung mit verdünnter Natronlauge versetzt, so entsteht zunächst ein Niederschlag des hellgelben Acetats, welcher bei weiterem Alkalizusatz dunkler wird und allmählich in eine feinkristallinische schwere, orangegelbe Masse übergeht.The reflux condenser was boiled in an oil bath for 30 hours, then the liquid was removed from the Precipitation separated and the latter by etherification or steam distillation of freed from the nitrotoluene suspended therein. In addition to the new mercury-silver compound, the product contains des ο - nitrotoluene, still unchanged mercury oxide and small amounts of mercury. The mixture is digested with 10 percent hydrochloric acid in the cold, which dissolves the mercury oxide and the reaction product is converted into its extremely poorly soluble light yellow chloride will. The free mercury compound is recovered from the latter by heating it with very dilute sodium hydroxide solution. Around To keep these completely pure, they are digested for a long time with excess cold 10 percent acetic acid and, after possible filtration, receives a light yellow clear solution, which contains the acetate of the new compound. If this solution is diluted with Sodium hydroxide solution is added, first a precipitate of the light yellow acetate is formed, which becomes darker with further addition of alkali and gradually becomes finely crystalline heavy, orange-yellow mass passes over.
Die so gereinigte Verbindung verpufft bei raschem Erhitzen; im Kapillarrohr erwärmt, zersetzt sie sich allmählich unter Dunkelfärbung oberhalb 2200 ohne zu schmelzen. Sie löst sich leicht in verdünnter Essigsäure und in 20 prozentiger Salpetersäure, in verdünnter Schwefelsäure ist sie schwerer löslich, in Salzsäure unlöslich.The compound purified in this way evaporates on rapid heating; heated in the capillary tube, it gradually decomposes with a dark color above 220 ° without melting. It dissolves easily in dilute acetic acid and in 20 percent nitric acid; in dilute sulfuric acid it is less soluble, and insoluble in hydrochloric acid.
Beim Ersatz der Natronlauge in obigem Beispiel durch Natriumcarbonat oder Kalk gelangt man zu demselben Produkt. Wird das Wasser durch verdünnten Alkohol ersetzt, so ist der Niederschlag sehr dunkel gefärbt und enthält größere Mengen von Nebenprodukten. Die alkalischen Lösungen enthalten stets noch geringe Mengen des Produkts gelöst, welche man am besten durchWhen replacing the caustic soda in the above example with sodium carbonate or lime one arrives at the same product. If the water is replaced by diluted alcohol, the precipitate is very dark in color and contains large amounts of by-products. The alkaline solutions always contain small amounts of the product dissolved, which is best done through
ίο Salzsäure daraus abscheidet. Aus diesen Fällungen lassen sich mit Ammoniak meist noch geringe Mengen der Monoquecksilberverbindung extrahieren, während das Diquecksilberprodukt von Ammoniak nicht aufgenommen wird. Mengenverhältnisse und Reaktionsdauer können innerhalb weiter Grenzen abgeändert werden, doch darf die Konzentration der Natronlauge nicht wesentlich erhöht werden, da die Verbindung durch stärkere Natronlaug zersetzt wird.ίο hydrochloric acid separates from it. From these Small amounts of the mono-mercury compound can usually be precipitated with ammonia extract while the mercury product of ammonia is not absorbed will. The proportions and duration of the reaction can be varied within wide limits, but the concentration is allowed the caustic soda can not be increased significantly because the connection is stronger Caustic soda is decomposed.
Die neue Verbindung soll zur Darstellung von Farbstoffen und Arzneimitteln Verwendung finden.The new compound is said to be used for the representation of dyes and medicines Find.
Claims (1)
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DE182218C true DE182218C (en) |
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ID=446336
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